A Gamble
by BloodBlackHeart
Summary: Will Damon take the gamble? Rated M - Dark themes
1. Chapter 1

DISCLAIMER: I DO NOT OWN THE VAMPIRE DIARIES OR ANY OF THE CHARACTERS

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><p>A Gamble – Part I<p>

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><p>Caroline was horny, angry and was feeling kind of dark. She figured it was a vampire thing. She needed an outlet and she decided to take a little revenge on Damon – but knowing the jackass, he'd probably love it...<p>

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><p>Damon's eyes opened slowly, he felt tired, weak and heavy. His wrists and ankles burned, his insides burned, he needed blood. Someone had vervained him obviously. He tried to move his arms but he couldn't. He moved his head to glance upwards and saw that his hands were tied above his head. He used all the strength he had and they wouldn't budge. He sighed irritated. Vervain soaked ropes. Typical.<p>

That's when he realised he was on a bed. He lifted his head and looked down at his body and noticed his legs were tied down too – oh, and he was completely naked. Perfect, he thought annoyed. He didn't recognise the room though he gathered that it was some kind of motel room.

"What the hell?" He yelled annoyed. Seconds later the bathroom door opened and out stepped a woman wearing a blood red corset with a black skirt that barely covered her ass, her curly dark red hair flowed down just past her shoulders and her face was covered with a masquerade mask, leaving only her mouth visible. He didn't recognise the person though he suddenly felt really turned on. She was hot. Really hot. "Who are you?" He asked but she said nothing. She wandered over to the bed while Damon watched. He was completely defenceless considering he couldn't get free _and _he was weak from all of the vervain.

Caroline saw the nervousness in his eyes. She saw that he was worried about the outcome. She'd put a wig on, she'd doused herself in cheap store perfume so that he wouldn't catch her scent. She put her hand on his leg near his ankle and Damon watched in half curiosity and half nervousness. She ran her hand achingly slowly up his leg and she saw his cock twitch. Her fingers travelled up past his knee, up his thigh and Damon visibly enjoyed where she seemed to be heading. She bypassed his cock and trailed her fingers over his hip bone, up his stomach over his toned muscles which shuddered at her touch and she circled his nipple with feather light ministrations of her fingertips. She bent her fingers a little then put her nails on his skin. Still gently she scratched her way back down his torso and he shivered at the sensation. As she got to his hip he groaned a little then his cock hardened so she continued to scratch down and bypassed his cock again but kept going down his leg until she arrived where she started.

Caroline then reached over to the bedside and grabbed a printed note she'd made. Damon watched curiously as she picked up the card then held it up for him to read.

_You have two choices at this point, Damon Salvatore._

_Choice One: All you have to say is 'Stop' and you will wake up in no time, untouched, at home in your bed and none of this ever happened._

_Choice Two: I do whatever I want to do to you and I do mean __whatever__. You only have to tell me that I have your consent._

_Will you play it safe? Or will you take a gamble?_

Damon read the card twice as she held it. This was seriously hot. He'd never experienced anything like this before. Though he _was _slightly concerned by the 'whatever' part considering – that basically meant she could kill him and he would have consented to it. _But, _he thought to himself, if she planned to kill him, she probably wouldn't have given him the option to opt out. He thought about it then he knew his answer. Stefan always said he had a gambling problem...

"I consent."


	2. Chapter 2

DISCLAIMER: I DO NOT OWN THE VAMPIRE DIARIES OR ANY OF THE CHARACTERS

**A/N: Thank you to starzee for being my beta! I forgot to say that last chapter!**

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><p>A Gamble – Part II<p>

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><p>Caroline thought this was highly amusing. He had no idea it was her and he'd basically just agreed to let her do anything she wanted to him. That was something she'd always wanted from him when she was human; her way with him. She set down the card on the bedside table then manoeuvred herself back to the bed. She crawled onto the bed then swung her leg over his stomach and straddled him.<p>

Damon watched in anticipation. He gathered by the note that the woman wasn't going to speak. He had a feeling he knew this person but he honestly couldn't guess who it was. She'd done an amazing job at covering her scent, her looks and with no speech he _genuinely _had no idea who it was. He wondered if it was maybe Katherine – she was into the games after all. His cock was throbbing for attention because this may have been the hottest thing he'd ever experienced.

Caroline bent down and grazed her tongue and teeth over his clavicle and she felt him shudder beneath her. She explored his chest with her mouth and fingernails and Damon was vocally enjoying it. She moved her way down his body slowly with her mouth and hands and every few minutes she shimmied down him a little more.

Damon saw where this was headed and he had to concentrate on not shooting his load straight away. Caroline sucked, licked and bit down his hips then took hold of his cock and trailed her tongue up his shaft while Damon moaned loudly at finally getting some contact. She swirled her tongue around the tip and was pleased at how turned on he clearly was considering he had leaked pre-cum already. She wrapped her hand around the base of his cock then moved it up and down, stroking him while she sucked and licked the tip. He shook a little beneath her because he felt so much pleasure in that moment. She wrapped her lips around his cock and bobbed her head a little while she continued to stroke him then with her other hand she cupped his balls and played with them while rolling her hand.

Damon groaned and moaned and holy hell it was amazing. He couldn't believe this was happening to him – he knew he wasn't going to last much longer.

"I'm... going to... cum." He sputtered and Caroline had to concentrate so she wouldn't laugh at him coming so undone. Caroline allowed her face to change, not that Damon noticed. She felt him tense underneath her and she bit down on his cock just as he came. "HOLY FUCK!" He screamed. The mixed pain and intense pleasure of having his blood drained that way was indescribable. Damon's eyes rolled into the back of his skull with the most amazing orgasm he'd ever had in his life and he came forcefully as Caroline swallowed down his cum and his blood. She licked him clean when he was finished and her face changed back before she climbed off of him.

Damon had no brain function after that. No other orgasm was ever going to top that. Caroline went over to the bedside cabinet and opened a drawer. She pulled out a flask, unscrewed the top then held it to Damon's lips. He had no idea what was in it but he couldn't really think straight so he opened his mouth. Caroline poured some of the liquid into Damon's mouth and as soon as it touched his tongue he moaned a little in pleasure considering it was blood mixed with bourbon. He swallowed hungrily and Caroline kept pouring it into his mouth – she needed him strong enough to get hard again...


	3. Chapter 3

DISCLAIMER: I DO NOT OWN THE VAMPIRE DIARIES OR ANY OF THE CHARACTERS

**A/N: Thanks to my beta starzee! Hope everyone had a nice Christmas! :) One chapter left!**

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><p>A Gamble – Part III<p>

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><p>"You have to tell me who you are." Damon said as she put the flask away but she ignored him again. As much as this <em>was <em>totally hot, Damon _really _wanted to know who she was. How the hell was he going to find her to have sex again if he didn't know who she was? Damon felt himself getting a little stronger so he tried getting himself free again but he still wasn't strong enough to do that and he sighed.

Caroline knew the next part was going to freak him out. She reached into the drawer and pulled out a sex toy. Damon stared at it in confusion as he had no _idea _what the hell she was going to do with _that_.

Originally, Caroline had wanted to take revenge on Damon – dominate him, make him helpless, use him, just like he'd done with her – then her plan changed. She wanted to make it _the _best sex he'd ever had so that it drove him crazy trying to figure out who the hell she was – she thought that would be more satisfying and amusing to watch. She'd gone to a sex shop and asked what would give a man the best orgasm of his life. They'd told her threefold stimulation – prostate, testicular _and _penile simultaneous stimulation – so she bought a sex toy that would stimulate the prostate and balls while she rode him.

"What the hell is that?" Damon asked wide eyed and she saw the mild panic on his face and it made her smirk. Damon saw her smirk and it only worried him _further_. Caroline took out a small bottle of lube and lathered it over the toy – that's when Damon figured out where it was going. "You have got to be kidding me." He said straight-faced and she shook with silent laughter which he noticed. His legs however were tied on opposite sides of the bed so there was _literally _nothing he could do about it. He was starting to rethink this 'anything' thing he agreed to. Caroline walked over to the bed and climbed between his legs. She took his soft cock with her hand and started to massage him.

Damon couldn't help his body's response and he started to harden again with a small moan. She moved the sex toy between his legs and stroked him a little faster. Damon thought about it for a second – she obviously knew what the hell she was doing. Before, if someone had asked him if he'd enjoy his cock being bitten the answer would have been 'HELL NO' but _that _had been his best orgasm ever. So... he decided to just let her do whatever she wanted. He'd already consented to that. He tried to relax as much as possible when he felt the toy press against him.

Caroline was surprised that he'd calmed himself. She saw that he was accepting it and that had her kind of amused. She let the toy gently slide inside him. It was fairly slim so she didn't think he'd feel any pain. Damon found it strange that it didn't hurt but it was kind of small so he wasn't really surprised. She positioned it the way she'd been told to then moved the other side against the underneath of his balls – then she flicked the switch and it started to vibrate.

"Fuck." Damon gasped at the amazing new sensation and Caroline smirked again. Damon saw it and now understood why she'd done it – it was fucking awesome. Caroline moved up his body and positioned his cock at her entrance and Damon groaned in anticipation – he now also understood that she had no underwear on under the tiny skirt and that turned him on immensely. She let his cock slide inside her and he cursed at the tightness.

Damon felt like he was in pleasure overload. The little device she'd set up was _genius_ and he couldn't believe he'd never tried anything like that before. Caroline's hand was behind her and she held the toy in place as she rode him. She increased her speed to half vampire speed and Damon sputtered at the fact he was now sure he was going to die of pleasure.

Caroline could feel the vibrations as she rode him and it made it even better. It was amazing. Caroline knew he wasn't going to last long again considering the guy in the shop told her it would be over fast and the orgasm he'd have would be enough to knock him out – she didn't think it would be enough to knock a vampire out but she was sure he wouldn't be able to go again so she worked her hips so that she would orgasm quickly. Moments later she felt her legs shake and she grew closer. Damon knew she was going to orgasm soon and honestly he thought he was going to die when his orgasm finally hit him – he knew it wouldn't be long. Caroline bit her lip as she came so that it was completely silent. Any sound at all from her could give away her identity and she so couldn't have him finding out it was her.

Caroline clamped her muscles tightly as she came and that was all it took for Damon – he came forcefully and he swore and groaned and shook and it was the _longest _and most euphoric orgasm he'd ever had...

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><p>Review?<p> 


	4. Chapter 4

DISCLAIMER: I DO NOT OWN THE VAMPIRE DIARIES OR ANY OF THE CHARACTERS

**A/N: Thanks to my beta starzee :) Last chapter!**

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><p>A Gamble – Part IV<p>

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><p>Damon panted as he tried to regain some semblance of coherence. Caroline was satisfied finally. She'd been so horny and her orgasm was amazing. She climbed off his lap then removed the sex toy from him and placed it back in the drawer.<p>

"Tell me your name." Damon gasped as he couldn't bear the thought of never having sex with this woman again. It had been so much better than anything he'd ever had before and he thought it would be a tragedy to never have her again. Caroline pulled something out of the drawer that Damon didn't quite see then she straddled his stomach again and looked down at him beneath her.

Caroline moved her hand up to stroke his cheek softly and Damon's expression was one she'd never seen on him before. He looked... vulnerable. He seemed to enjoy the softness of that momentary affection though it was obvious that he was trying _not _to enjoy it. She leaned down and placed a kiss on his lips and she was surprised when he kissed her back. He tried to deepen the kiss but she pulled back up to look at him. She still had her hand on his cheek and she grazed her thumb lightly over the skin there.

Damon had a realisation in that moment. This person cared about him. Someone could never do something so affectionate if they didn't.

Caroline then revealed her other hand and Damon saw a needle and he knew what was in it. His eyes widened and he was about to protest but she slid it gently into his arm.

"No." He said confused as he really needed more time to try to figure out who the hell she was then his vision started to fade and he felt the burn and seconds later it was all black.

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><p>Damon's eyes opened and he sat up immediately. He looked around and he saw that he was in his room. He was fully dressed.<p>

"That wasn't a dream." He said out loud because he could still feel the burn of the vervain. He turned his head and looked at the bed and he noticed a red envelope with a black ribbon tied around it sitting there. He scrambled for it and pulled the ribbon off. He lifted the flap and pulled out the little white card and read.

_You took the gamble. You're a brave man, Damon Salvatore. I thoroughly enjoyed our little game. Perhaps one day I'll kidnap you again. _

_Would you say you won or lost in this gamble?_

Damon scowled at the small card. He couldn't answer the question. On the one hand, it had been the best sex of his existence, on the other hand, he had no idea who it was with, he had no idea how to find her, he just had no idea.

"Dammit." He muttered.

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><p>Caroline noticed that Damon had been extra agitated for months since her little kidnapping game. She knew he'd been looking. She knew he'd been assessing who it could be. She found it highly amusing. He'd asked her questions and she'd prepared for that so she 'played dumb'. He'd asked the other vampires questions – Elena, Katherine... they had no idea either. She overheard him tell Ric about it – though he left out the sex toy part which amused her.<p>

The months went by and Damon came to the conclusion that she knew he was looking for her and she was playing with him. Not letting him know who it was. That really annoyed him – he felt a little obsessed.

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><p>Six months after she'd kidnapped him, she decided to put him out of his misery. She'd hung out with Stefan and Elena in the boarding house and just as she was leaving the house, Damon came in the door.<p>

"Hey, Blondie." He said and she smirked at him then walked past him to the door and looked over her shoulder.

"Hey, Damon?" She asked and he turned to look at her from down the hall.

"What?" He asked her curiously.

"Do you like to gamble?" She asked him teasingly and his eyes widened and his jaw dropped with the realisation. He blinked rapidly just as she gave him that seductive sexy smirk she'd given him all those months ago and he recognised it. He got flashbacks of her mask covered face. He knew that sexy smirk.

"It was... you." He said and the shock was written all over his face and she chuckled.

"Later, Damon." She winked then vanished out the door closing it behind her – leaving Damon in the hall staring at the door with his mouth gaping wide at the fact _Blondie _had vervained him, kidnapped him, tied him up then had given him the best sex of his life...

"Holy. Fuck." Damon gasped.

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><p><strong>The End<strong>

Sequel? No Sequel?


	5. Sequel

**Thank you so much to everyone who reviewed this story!**

**It means so much to me, it really does.**

**I have started writing a sequel to it but I'd love your opinions.**

**'A Gamble' was just smut, really, though the sequel I've been writing has plot too...**

**So my question is this:**

**Would you like to read a sequel to this where it is written just as another smutty encounter...**

**OR**

**Would you like a story with some plot?**

**Please let me know what you'd like to read and I'll get on that :)**

**Thanks again!**

**BloodBlackHeart**

**-x-x-x-**


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